Application

No.104
Phosphorylation
D2624 Dibenzyl N,N-Diisopropylphosphoramidite (1) 5g

The present reagent 1 reacts rapidly with alcohols in the presence of 1H-tetrazole at room temperature to generate phosphorous triesters. Subsequent reaction with oxidizing agents such as m-chloroperoxybenzoic acid affords the corresponding phosphoric triesters 2. The triesters thus obtained can be deprotected by cleavage of the benzyl group by catalytic hydrogenolysis using Pd/C to yield the desired derivatives of phosphoric acids 31). The reagent 1 has high reactivity and its reactions to proceed under mild conditions. It has a wide scope of applications, including the synthesis of biomolecules such as oligonucleotides2).

References

1) Phosphorylation of cyclitols
K.-L. Yu, B. Fraser-Reid, Tetrahedron Lett., 29, 979 (1988).
2) The synthesis of oligonucleotides
S. L. Beaucage, R. P. Iyer, Tetrahedron, 48, 2223 (1992).
3) Other applications
a) Phosphorylation of amino acids
W. Bannwarth, A. Trzeciak, Helv. Chim. Acta, 70, 175 (1987).
b) Phosphorylation of peptides
J. W. Perich, R. B. Johns, Tetrahedron Lett., 29, 2369 (1988).
c) Phosphorylation of sugars
Y. Ichikawa, M. M. Sim, C.-H. Wong, J. Org. Chem., 57, 2943 (1992).

Related Compounds

C0978 Barium 2-Cyanoethylphosphate 25g
5g
C1210 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one 25g
5g
C1215 2-Chloro-1,3,2-dioxaphospholane 25g
C1250 2-Chloro-2-oxo-1,3,2-dioxaphospholane 10g
C1018 2-Chlorophenyl-N-phenylphosphoramidochloridate 25g
5g
C1019 4-Chlorophenyl-N-phenylphosphoramidochloridate 25g
5g
C0976 2-Chlorophenylphosphorodichloridate 25g
5g
C0977 4-Chlorophenylphosphorodichloridate 25g
5g
D1613 S,S'-Diphenylphosphorodithioate Monocyclohexylammonium Salt 25g
5g
D1059 Diphenylphosphoryl Chloride 500g
25g
M0904 Methyl Phosphorodichloridate 25g
M0905 Methyl Phosphorodichloridite 10g
P0209 Phenylphosphoryl Dichloride 500g
25g
P1223 Pyrophosphoric Acid Tetrabenzyl Ester 1g
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